US2887465A - Stabilization of chlorine containing polymers with (epoxyethyl) benzenes - Google Patents
Stabilization of chlorine containing polymers with (epoxyethyl) benzenes Download PDFInfo
- Publication number
- US2887465A US2887465A US714079A US71407958A US2887465A US 2887465 A US2887465 A US 2887465A US 714079 A US714079 A US 714079A US 71407958 A US71407958 A US 71407958A US 2887465 A US2887465 A US 2887465A
- Authority
- US
- United States
- Prior art keywords
- epoxyethyl
- benzene
- chlorine containing
- benzenes
- stabilization
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1515—Three-membered rings
Definitions
- epoxy compounds such as, for example phenoxy propene oxide or glycide ethers of phenols as stabilising agents for such compounds has already been suggested.
- liquid substances are meant in which the epoxy group is bound to the aromatic nucleus by way of an oxygen atom.
- solid polyepoxy compounds containing the epoxy group linked direct to the aromatic nucleus are excellently suitable for the stabilisation of halogen-containing macromolecular compounds, in particular polyvinyl chloride, polyvinylidene chloride, chlorinated rubber and mixed polymers containing vinyl chloride or vinylidene chloride, as well as polychlorinated diphenyls and polychloronaphthalenes.
- polyepoxides are 1.3- or 1.4-di-(epoxyethyl) -benzene or 1.3.5-tri-(epoxyethyl)-benzene of the following formulae:
- the new, heat stable compositions according to the present invention contain 0.1 to about 3% of the stabilisers, which amount is absolutely sulficient to attain a great improvement of the stability to heat of the products.
- the poly- 2,887,465 Patented May 19, 1959 epoxides mentioned can also be used for the stabilising of solutions of the macromolecular halogen compounds in organic solvents.
- Example 1 100 parts of a polymer obtained by emulsion polymerisation of vinyl chloride are mixed in powder form with 0.5 part of 1.3.5-tri-(epoxyethyl)-benzene in a ball mill. On plasticising on a hot roller mill and then pressing, sheets having excellent stability to heat are obtained.
- Example 2 A mixed polymer from parts of vinylidene chloride and 15 parts of vinyl chloride, obtained by emulsion polymerisation is mixed with 1 part of 1.3.5-tri-(epoxyethyl) -benzene in a ball mill and then formed into bristles or little bands in an alloy extruder containing no iron. The products obtained are very light coloured and have good stability to heat.
- Example 3 A 20% solution of chlorinated rubber which also contains 0.5% of l.4-di-(epoxyethyl)-benzene in toluene solution (calculated on the chlorinated rubber) is poured into a film. After drying, the film produced has very good stability to heat and weather.
- Example 4 parts of an emulsion polymer of vinyl chloride are mixed with 2.5 parts of the di-epoxide from technical divinyl benzene, consisting of about 70% of the meta and 30% of the para compound, 30 parts of dioctyl phthalate are added and the whole is rolled on a heated calender into a homogeneous foil.
- the product so obtained can be made into elastic forms which have excellent stability to heat.
- the new heat stable composition of matter consisting essentially of a chlorine containing macromolecular com pound selected from the group consisting of polyvinyl chloride, polyvinylidene chloride and chlorinated rubber and of from 0.1 to 3%, calculated on said compound, of a solid stabiliser selected from the group consisting of 1 .3-di-( epoxyethyl) -benzene, 1.4-di-(epoxyethy1) -benzene and l.3.5-tri-(epoxyethyl)-benzene.
- the new heat stable composition of matter consisting essentially of polyvinyl chloride and of from 0.5 to 1%, calculated on said compound, of 1.3.5-tri-(epoxyethyl) -b enzene.
- the new heat stable composition of matter consisting essentially of polyvinylidene chloride and of from 0.5 to 1%, calculated on said compound, of 1.3.5-tri- (epoxyethyl) -benzene.
- the new heat stable composition of matter consisting essentially of chlorinated rubber and of from 0.5 to 1%, calculated on said compound, of 1.4-di-(epoxyethy1)- benzene.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH875017X | 1957-02-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2887465A true US2887465A (en) | 1959-05-19 |
Family
ID=4544323
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US714079A Expired - Lifetime US2887465A (en) | 1957-02-14 | 1958-02-10 | Stabilization of chlorine containing polymers with (epoxyethyl) benzenes |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2887465A (de) |
| CH (1) | CH351749A (de) |
| DE (1) | DE1168071B (de) |
| GB (1) | GB875017A (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3251861A (en) * | 1966-05-17 | Di- and triepoxtoe derivatives of trivinylcyclohexane |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101616898B1 (ko) * | 2009-03-05 | 2016-04-29 | 신닛테츠 수미킨 가가쿠 가부시키가이샤 | 에폭시 수지 조성물 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2595619A (en) * | 1948-03-04 | 1952-05-06 | Shell Dev | Use of a mixture of a diamide of a carbonic acid and an epoxy compound to stabilize a halogen containing material |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE611380C (de) * | 1932-04-22 | 1935-03-27 | I G Farbenindustrie Akt Ges | Verfahren zur Stabilisierung von Chlorierungsprodukten hoehermolekularer Substanzen,insbesondere Chlorkautschuk |
| DE656133C (de) * | 1933-12-07 | 1938-01-29 | I G Farbenindustrie Akt Ges | Verfahren zur Stabilisierung von Polyvinylchlorid |
| NL66626C (de) * | 1946-09-26 | 1950-11-15 |
-
1957
- 1957-02-14 CH CH351749D patent/CH351749A/de unknown
-
1958
- 1958-02-10 US US714079A patent/US2887465A/en not_active Expired - Lifetime
- 1958-02-13 GB GB4725/58A patent/GB875017A/en not_active Expired
- 1958-02-13 DE DEG23910A patent/DE1168071B/de active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2595619A (en) * | 1948-03-04 | 1952-05-06 | Shell Dev | Use of a mixture of a diamide of a carbonic acid and an epoxy compound to stabilize a halogen containing material |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3251861A (en) * | 1966-05-17 | Di- and triepoxtoe derivatives of trivinylcyclohexane |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1168071B (de) | 1964-04-16 |
| GB875017A (en) | 1961-08-16 |
| CH351749A (de) | 1961-01-31 |
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